New opportunities for the use of alpha-lipoic acid: the role of enantiomers

Authors

  • T.Yu. Yuzvenko MD, PhD, Deputy Director, Ukrainian Research and Practice Center of Endocrine Surgery, Transplantation of Endocrine Organs and Tissues of the Ministry of Health of Ukraine, Kyiv, Ukraine http://orcid.org/0000-0003-4229-2075
  • S.A. Tarasenko PhD, Anesthesiologist, Department of prophylaxis and treatment of diabetes, Ukrainian Research and Practice Center of Endocrine Surgery, Transplantation of Endocrine Organs and Tissues of the Ministry of Health of Ukraine, Kyiv, Ukraine http://orcid.org/0000-0001-9970-4574
  • O.V. Marchenko Endocrinologist, Department of prophylaxis and treatment of diabetes, Ukrainian Research and Practice Center of Endocrine Surgery, Transplantation of Endocrine Organs and Tissues of the Ministry of Health of Ukraine, Kyiv, Ukraine http://orcid.org/0000-0002-8040-9687

DOI:

https://doi.org/10.22141/2224-0721.15.6.2019.185414

Keywords:

alpha-lipoic acid, enantiomers, review

Abstract

The literature review considers the use of alpha-li­poic acid (ALA) in clinical practice. The positive effects of ALA as an antioxidant have been demonstrated for a wide range of diseases: diabetic neuropathy, atherosclerosis, hepatitis, cerebrovascular disorder, etc. The new data on the application of the R(+) enantiomer ALA has proved positive biological effects of ALA using. The only R(+) enantiomer ALA realizes all ALA positive features. The R(+) enantiomers of alpha-lipoic acid have the highest peak of plasma concentrations and AUC compared with racemic mixtures. It was showed that 300 mg of R(+) enantiomer of ALA is bioequivalent to 600 mg of racemic ALA.

Downloads

Download data is not yet available.

References

Reed LJ, Debusk BG, Gunsalus IC, Hornberger CS Jr. Crystalline alpha-lipoic acid a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. doi: 10.1126/science.114.2952.93.

Liu C, Feng X, Li Q, Wang Y, Li Q, Hua M. Adiponectin, TNF-alpha and inflammatory cytokines and risk of type 2 diabetes: a systematic review and meta-analysis. Cytokine. 2016 Oct;86:100-109. doi: 10.1016/j.cyto.2016.06.028.

Khalimov IuSh, Salukhov VV. Thioctic acid: from cellular regulatory mechanisms to clinical practice. Effektivnaia farmakoterapiia. Endokrinologiia. 2012;(2):22-28. (in Russian).

McIlduff CE, Rutkove SB. Critical appraisal of the use of alpha lipoic acid (thioctic acid) in the treatment of symptomatic diabetic polyneuropathy. Ther Clin Risk Manag. 2011;7:377-85. doi: 10.2147/TCRM.S11325.

Akbari M, Ostadmohammadi V, Tabrizi R, et al. The effects of alpha-lipoic acid supplementation on inflammatory markers among patients with metabolic syndrome and related disorders: a systematic review and meta-analysis of randomized controlled trials. Nutr Metab (Lond). 2018 Jun 5;15:39. doi: 10.1186/s12986-018-0274-y.

Murashko NK. Possibilities of using alpha-lipoic acid in the treatment of ischemic brain lesions. Meždunarodnyj nevrologičeskij žurnal. 2010;(35):28-34. (in Russian).

Pankiv IV. Efficiency of Alpha Lipoic Acid Therapy at Diabetic Foot Syndrome. Mìžnarodnij endokrinologìčnij žurnal. 2014;(59):53-55. doi: 10.22141/2224-0721.3.59.2014.76603. (in Ukrainian).

McNeilly AM, Davison GW, Murphy MH, et al. Effect of alpha-lipoic acid and exercise training on cardiovascular disease risk in obesity with impaired glucose tolerance. Lipids Health Dis. 2011 Nov 22;10:217. doi: 10.1186/1476-511X-10-217.

Sardu C, Santulli G, Santamaria M, et al. Effects of alpha lipoic acid on multiple cytokines and biomarkers and recurrence of atrial fibrillation within 1 year of catheter ablation. Am J Cardiol. 2017 May 1;119(9):1382-1386. doi: 10.1016/j.amjcard.2017.01.040.

Fornoni A, Ijaz A, Tejada T, Lenz O. Role of inflammation in diabetic nephropathy. Curr Diabetes Rev. 2008 Feb;4(1):10-7. doi: 10.2174/157339908783502361.

Karkabounas S, Papadopoulos N, Anastasiadou C, et al. Effects of α-Lipoic Acid, Carnosine, and Thiamine Supplementation in Obese Patients with Type 2 Diabetes Mellitus: A Randomized, Double-Blind Study. J Med Food. 2018 Dec;21(12):1197-1203. doi: 10.1089/jmf.2018.0007.

Callaghan BC, Cheng HT, Stables CL, Smith AL, Feldman EL. Diabetic neuropathy: clinical manifestations and current treatments. Lancet Neurol. 2012 Jun;11(6):521-34. doi: 10.1016/S1474-4422(12)70065-0.

Davies M, Brophy S, WilliamsR, Taylor A. The prevalence, severity, and impact of painful diabetic peripheral neuropathy in type 2 diabetes. Diabetes Care. 2006 Jul;29(7):1518-22. doi: 10.2337/dc05-2228.

Figueroa-Romero C, Sadidi M, Feldman EL. Mechanisms of disease: the oxidative stress theory of diabetic neuropathy. Rev Endocr Metab Disord. 2008 Dec;9(4):301-14. doi: 10.1007/s11154-008-9104-2.

Tesfaye S, Selvarajah D. Advances in the epidemiology, pathogenesis and management of diabetic peripheral neuropathy. Diabetes Metab Res Rev. 2012 Feb;28 Suppl 1:8-14. doi: 10.1002/dmrr.2239.

Kempler P, Tesfaye S, Chaturvedi N, et al. Autonomic neuropathy is associated with increased cardiovascular risk factors: the EURODIAB IDDM Complications Study. Diabet Med. 2002 Nov;19(11):900-9. doi: 10.1046/j.1464-5491.2002.00821.x.

Vinik AI, Maser RE, Mitchell BD, Freeman R. Diabetic Autonomic Neuropathy. Diabetes Care. 2003 May;26(5):1553-79. doi: 10.2337/diacare.26.5.1553.

AlOlaiwi LA, AlHarbi TJ, Tourkmani AM. Prevalence of cardiovascular autonomic neuropathy and gastroparesis symptoms among patients with type 2 diabetes who attend a primary health care center. PLoS One. 2018 Dec 21;13(12):e0209500. doi: 10.1371/journal.pone.0209500.

Dyck PJ, Davies JL, Litchy WJ, O'Brien PC. Longitudinal assessment of diabetic polyneuropathy using a composite score in the Rochester Diabetic Neuropathy Study cohort. Neurology. 1997 Jul;49(1):229-39. doi: 10.1212/wnl.49.1.229.

Mankovsky BN. The treatment of diabetic polyneuropathy: what is evidence base? Liky Ukrai'ny. 2011;(156):30-33. (in Russian).

Tesfaye S, Boulton AJM, Dyck PJ, et al. Diabetic neuropathies: update on definitions, diagnostic criteria, estimation of severity, and treatments. Diabetes Care. 2010 Oct;33(10):2285-93. doi: 10.2337/dc10-1303.

Dubrov SO, Tarasenko SO. Searching the optimal composition: combination pharmacotherapy of painful diabetic neuropathy. Clinical endocrinology and endocrine surgery. 2017;(59):13-20. doi: 10.24026/1818-1384.3(59).2017.110884. (in Ukrainian).

Ziegler D. Thioctic acid for patients with symptomatic diabetic polyneuropathy: a critical review. Treat Endocrinol. 2004;3(3):173-89. doi: 10.2165/00024677-200403030-00005.

Carlson DA, Smith AR, Fischer SJ, Young KL, Packer L. The plasma pharmacokinetics of R-(+)-lipoic acid administered as sodium R-(+)-lipoate to healthy human subjects. Altern Med Rev. 2007 Dec;12(4):343-51.

Zehnpfennig B, Wiriyasermkul P, Carlson DA, Quick M. Interaction of α-Lipoic Acid with the Human Na+/Multivitamin Transporter (hSMVT). J Biol Chem. 2015 Jun 26;290(26):16372-82. doi: 10.1074/jbc.M114.622555.

Ziegler D, Hanefeld M, Ruhnau KJ, et al. Treatment of symptomatic diabetic peripheral neuropathy with the anti-oxidant alpha-lipoic acid. A 3-week multicentre randomized controlled trial (ALADIN Study). Diabetologia. 1995 Dec;38(12):1425-33. doi: 10.1007/bf00400603.

Ziegler D, Hanefeld M, Ruhnau K, et al. Treatment of symptomatic diabetic polyneuropathy with the antioxidant alpha-lipoic acid: a 7-month multicenter randomized controlled trial (ALADIN III Study). ALADIN III Study Group. Alpha-Lipoic Acid in Diabetic Neuropathy. Diabetes Care. 1999 Aug;22(8):1296-301. doi: 10.2337/diacare.22.8.1296.

Berkson BM. A conservative triple antioxidant approach to the treatment of hepatitis C. Combination of alpha lipoic acid (thioctic acid), silymarin, and selenium: three case histories. Med Klin (Munich). 1999 Oct 15;94 Suppl 3:84-9. doi: 10.1007/bf03042201.

Zhang WJ, Bird KE, McMillen TS, LeBoeuf RC, Hagen TM, Frei B. Dietary alpha-lipoic acid supplementation inhibits atherosclerotic lesion development in apolipoprotein E-deficient and apolipoprotein E/low-density lipoprotein receptor-deficient mice. Circulation. 2008 Jan 22;117(3):421-8. doi: 10.1161/CIRCULATIONAHA.107.725275.

Sztanek F, Seres I, Lorincz H, Molnar A, Paragh G. Effect of alpha-lipoic acid supplementation on oxidative stress markers and antioxidative defense in patients with diabetic neuropathy. Atherosclerosis. 2017;(263):e111-e282. doi: 10.1016/j.atherosclerosis.2017.06.852.

Ying Z, Kherada N, Farrar B, et al. Lipoic acid effects on established atherosclerosis. Life Sci. 2010 Jan 16;86(3-4):95-102. doi: 10.1016/j.lfs.2009.11.009.

Papanas N, Ziegler D. Efficacy of α-lipoic acid in diabetic neuropathy. Expert Opin Pharmacother. 2014 Dec;15(18):2721-31. doi: 10.1517/14656566.2014.972935.

Hermann R, Mungo J, Cnota PJ, Ziegler D. Enantiomer-selective pharmacokinetics, oral bioavailability, and sex effects of various alpha-lipoic acid dosage forms. Clin Pharmacol. 2014 Nov 28;6:195-204. doi: 10.2147/CPAA.S71574.

Yoon J, Moon SJ, Lee KO, et al. Comparison of R(+)-α-lipoic acid exposure after R(+)-α-lipoic acid 200 mg and 300 mg and thioctic acid 600 mg in healthy Korean male subjects. Transl Clin Pharmacol. 2016;24(3):137-142. doi: 10.12793/tcp.2016.24.3.137.

Carlson DA, Young KL, Fischer SJ, Ulrich H. An Evaluation of the Stability and Pharmacokinetics of R-lipoic Acid and R-Dihydrolipoic Acid Dosage Forms in Plasma from Healthy Human Subjects. In: Packer L, Patel M, editors. Lipoic Acid: Energy Production, Antioxidant Activity and Health Effects. London, England: Taylor&Francis Publishers; 2008. 235-270 pp.

Published

2021-09-01

How to Cite

Yuzvenko, T., Tarasenko, S., & Marchenko, O. (2021). New opportunities for the use of alpha-lipoic acid: the role of enantiomers. INTERNATIONAL JOURNAL OF ENDOCRINOLOGY (Ukraine), 15(6), 507–514. https://doi.org/10.22141/2224-0721.15.6.2019.185414

Issue

Section

Literature Review

Most read articles by the same author(s)

1 2 > >>